Synthesis, antibacterial and antimycobacterial activities of some new 4-aryl/heteroaryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyridines

A novel class of 4-aryl/heteroaryl-2,6-dimethyl-3,5-bis-N-(phenyl/substituted phenyl)-carbamoyl-1,4-dihydropyridines has been synthesized by simple, economical and eco-friendly, modified Hantzsch condensation reaction making use of N-arylacetoacetamides, aryl or heteroaryl aldehydes and ammonium acetate. The newly synthesized compounds were characterized by their spectral (IR, H-1 NMR, Mass), elemental analyses data and evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv ATCC 27294 and antibacterial activity against different Gram +ve and Gram -ve bacteria. The preliminary screening results revealed that some of the compounds possess promising antimicrobial activity. Amongst the new series of compounds, 6m containing pyrrolyl and 4-methyl-phenyl groups and 6r possessing 2-pyridyl and 2-methylphenyl groups were found to exhibit a significant antitubercular activity (MIC = 12.5-25 mu g/mL) in comparison with the first line drug pyrazinamide. (C) 2011 Elsevier Masson SAS. All rights reserved.